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(S)-2,3-epoxysqualene

Go to external page http://purl.obolibrary.org/obo/CHEBI_15441

A 2,3-epoxysqualene in which the chiral centre has S configuration. It is converted to lanosterol by lanosterol synthase (EC 5.4.99.7) in a key rate-limiting step in the biosynthesis of chloesterol, steroid hormones, and vitamin D.

Term info

Label

(S)-2,3-epoxysqualene

Synonyms
  • (3S)-2,2-dimethyl-3-[(3E,7E,11E,15E)-3,7,12,16,20-pentamethylhenicosa-3,7,11,15,19-pentaen-1-yl]oxirane
  • (S)-2,3-Epoxysqualene
  • (S)-2,3-epoxysqualene
database cross reference
Subsets

3_STAR

IUPAC NAME
(3S)-2,2-dimethyl-3-[(3E,7E,11E,15E)-3,7,12,16,20-pentamethylhenicosa-3,7,11,15,19-pentaen-1-yl]oxirane [ IUPAC ]

charge

0

formula

C30H50O

has alternative id

CHEBI:372, CHEBI:11072, CHEBI:11026, CHEBI:18728

has obo namespace

chebi_ontology

has related synonym

2,3-epoxisqualene, (3S)-2,3-epoxy-2,3-dihydrosqualene, Squalene 2,3-oxide, (S)-Squalene-2,3-epoxide, (S)-2,3-epoxy-2,3-dihydrosqualene, (S)-squalene-2,3-epoxide, (S)-2,3-dihydro-2,3-epoxysqualene, Squalene 2,3-epoxide, oxidosqualene, (S)-2,3-oxidosqualene, 2,3-oxidosqualene, (3S)-2,3-dihydro-2,3-epoxysqualene, 2,3-EDSQ

id

CHEBI:15441

inchi

InChI=1S/C30H50O/c1-24(2)14-11-17-27(5)20-12-18-25(3)15-9-10-16-26(4)19-13-21-28(6)22-23-29-30(7,8)31-29/h14-16,20-21,29H,9-13,17-19,22-23H2,1-8H3/b25-15+,26-16+,27-20+,28-21+/t29-/m0/s1

inchikey

QYIMSPSDBYKPPY-RSKUXYSASA-N

mass

426.71740

monoisotopicmass

426.38617

smiles

CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C=C(/C)CC\C=C(/C)CC[C@@H]1OC1(C)C